Disperse azo dyes, a process for the preparation thereof and the use thereof

Abstract

The present invention relates to azo dyes of formula (1), wherein D is a radical of formula (2) or (3), R.sub.1 and R.sub.2 independently denote hydrogen; C.sub.6-C.sub.10 aryl which is unsubstituted or substituted by cyano, carboxy, hydroxy, halogen, C.sub.1-C.sub.6alkyl, or C.sub.1-C.sub.6alkoxy; C.sub.1-C.sub.12alkyl which may be interrupted one or more times by O, S, NR.sub.4, CO, COO or OOC, and is unsubstituted or substituted by cyano, carboxy, hydroxy, C.sub.6-C.sub.10 aryl, or C.sub.6-C.sub.10 aryloxy, which C.sub.6-C.sub.10 aryl or C.sub.6-C.sub.10 aryloxy is unsubstituted or substituted by cyano, carboxy, hydroxy, halogen, C.sub.1-C.sub.6alkyl, or C.sub.1-C.sub.6alkoxy; R.sub.3 and R.sub.4 are each independently of the other hydrogen, halogen, nitro, cyano, trifluoromethyl, carboxy, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6alkylcarbonyl, C.sub.6-C.sub.10 arylcarbonyl, C.sub.1-C.sub.6alkoxycarbonyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.1-C.sub.6alkylsulfonylamino or C.sub.1-C.sub.4 alkanoylamino; and R.sub.5 is halogen, nitro, cyano, trifluoromethyl, carboxy, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6alkylcarbonyl, C.sub.6-C.sub.10 arylcarbonyl, C.sub.1-C.sub.6alkoxycarbonyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.1-C.sub.6alkylsulfonylamino or C.sub.1-C.sub.4 alkanoylamino; and R.sub.6, R.sub.7, R.sub.8 and R.sub.9 independently of each other are hydrogen, hydroxy, halogen, cyano, nitro or C.sub.1-C.sub.4 alkanoylamino, and the radicals X independently denote N or CH, with the proviso that at least one radical X denotes CH, which are distinguished by their good lightfastness properties. ##STR00001##

Claims

1. An azo dye of formula ##STR00129## wherein D is a radical of formula ##STR00130## R.sub.1 and R.sub.2 independently denote hydrogen; C.sub.6-C.sub.10 aryl which is unsubstituted or substituted by cyano, carboxy, hydroxy, halogen, C.sub.1-C.sub.6alkyl, or C.sub.1-C.sub.6alkoxy; C.sub.1-C.sub.12alkyl which may be interrupted one or more times by O, S, NR.sub.4, CO, COO or OOC, and is unsubstituted or substituted by cyano, carboxy, hydroxy, C.sub.6-C.sub.10 aryl, or C.sub.6-C.sub.10 aryloxy, which C.sub.6-C.sub.10 aryl or C.sub.6-C.sub.10 aryloxy is unsubstituted or substituted by cyano, carboxy, hydroxy, halogen, C.sub.1-C.sub.6 alkyl, or C.sub.1-C.sub.6 alkoxy; R.sub.3 and R.sub.4 are each independently of the other hydrogen, halogen, nitro, cyano, trifluoromethyl, carboxy, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 alkylcarbonyl, C.sub.6-C.sub.10 arylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6 alkylsulfonylamino or C.sub.1-C.sub.4 alkanoylamino, and R.sub.5 is halogen, nitro, cyano, trifluoromethyl, carboxy, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 alkylcarbonyl, C.sub.6-C.sub.10 arylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6 alkylsulfonylamino or C.sub.1-C.sub.4 alkanoylamino; and R.sub.6, R.sub.7, R.sub.8 and R.sub.9 independently of each other are hydrogen, hydroxy, halogen, cyano, nitro or C.sub.1-C.sub.4 alkanoylamino, and the radicals X independently denote N or CH, with the proviso that at least one radical X denotes CH.

2. An azo dye of formula (1) according to claim 1, wherein R.sub.1 and R.sub.2 independently denote hydrogen, methyl, ethyl, n-propyl, i-propyl or n-butyl, 2-methoxyethyl, 3-methoxypropyl, 4-methoxybutyl, 2-ethoxyethyl, 3-ethoxypropyl, 4-ethoxybutyl, phenyl, tolyl, benzyl, or 2-phenylethyl.

3. An azo dye of formula (1) according to claim 1, wherein R.sub.1 is hydrogen and R.sub.2 denotes hydrogen, methyl, ethyl, n-propyl, i-propy n-butyl, 2-methoxyethyl, 3-methoxypropyl, 4-methoxybutyl, 2-ethoxyethyl, 3-ethoxypropyl, 4-ethoxybutyl, phenyl, tolyl, benzyl, or 2-phenylethyl.

4. An azo dye of formula (1) according to claim 1, wherein R.sub.1 and R.sub.2 are hydrogen.

5. An azo dye of formula (1) according to claim 1, wherein both radicals X denote CH.

6. An azo dye of formula (1) according to claim 1, wherein R.sub.3 and R.sub.4 are each independently of the other hydrogen, halogen, nitro, cyano, trifluoromethyl, methylsulfonyl, ethylsulfonyl, acetylamino, or propionylamino and wherein R.sub.5 is halogen, nitro, cyano, trifluoromethyl, methylsulfonyl, ethylsulfonyl, acetylamino, or propionylamino.

7. An azo dye of formula (1) according to claim 6, wherein R.sub.3 and R.sub.4 are each independently of the other hydrogen, halogen, nitro, cyano, or trifluoromethyl and wherein R.sub.5 is halogen, nitro, cyano, or trifluoromethyl.

8. An azo dye of formula (1) according claim 1, wherein R.sub.6, R.sub.7, R.sub.8 and R.sub.9 independently of each other are hydrogen, hydroxy, halogen, acetylamino, or propionylamino.

9. An azo dye of formula (1) according to claim 1, wherein D is a radical of formula (2).

10. A process for the preparation of an azo dye of formula (1) according to claim 1, which comprises diazotizing an amine compound of formula ##STR00131## to form a diazotized amine and then coupling the diazotized amine to a coupling component of the formula ##STR00132## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9 and X are as defined in claim 1.

11. A process for dyeing semi-synthetic or synthetic hydrophobic fibre materials comprising applying an aqueous composition comprising a dye of formula (1) according to claim 1 to the semi-synthetic or synthetic hydrophobic fibre materials.

12. A semi-synthetic or synthetic hydrophobic fibre material, dyed by the process according to claim 11.

13. A process for printing semi-synthetic or synthetic fibre materials comprising spraying an aqueous composition comprising a dye of formula (1) according to claim 1 onto the semi-synthetic or synthetic hydrophobic fibre materials.

14. A semi-synthetic or synthetic hydrophobic fibre material printed by the process according to claim 13.

Description

COMPARATIVE EXAMPLES

(1) Application Example 1 is repeated by using a dye disclosed in GB 1418742. The dyes disclosed in GB 1418742 are corresponding to substituted diamino pyrimidine disperse azo dyes but GB 1418742 fails to disclose diamino pyrimidine disperse azo dyes substituted with a nitrogen containing heterocyclic aromatic ring. Examples of dyes disclosed in GB 1418742 and used in this Comparative Example 1 and Comparative Example 2 are according to following structure:

(2) ##STR00125##

Comparative Example 1

(3) ##STR00126##

Comparative Example 2

(4) The light fastness and colour change after heat-light exposure obtained using the dye according to GB 1418742 was compared to the light fastness obtained using the dye according to Application Example 22 and Application Example 24:

(5) ##STR00127##

Application Example 22

(6) ##STR00128##

Application Example 24

(7) The results obtained according to the SAE J2412 488 kJ standard are summarized below:

(8) TABLE-US-00002 Colour colour strength change Build After After Up exposure exposure (RD) (%) dE.sub.ab* Comparative example 1 0.25 74 6.33 Application example 22 0.25 77 4.92 Comparative example 2 0.25 61 10.66 Application example 24 0.25 69 8.42

(9) The loss of colour strength after heat-light exposure according to the SAE J2412 488 kJ test using the dye according to the invention (corresponding to preparation example 22) is slightly better compared to the loss of colour strength using the dye according to GB 1418742.

(10) The colour change (dE.sub.ab* or dE* in short form) is calculated according the following formula:
dE.sub.ab*=((dL*).sup.2+(da*).sup.2+(db*).sup.2).sup.1/2

(11) Wherein a*, b*=colour coordinates da*, db*=difference of the colour coordinates L*=lightness dL*=change of the lightness

(12) The colour change after heat-light exposure according to the SAE J2412 488 kJ test using the dye according to the invention (corresponding to preparation example 22) is significantly better compared to the colour change using the dye according to GB 1418742. This surprising result is due to the presence of the substituted nitrogen containing heterocyclic aromatic ring in the dye according to the invention.